While the Boss is Away

How to Support Your Exec Before, During, and After Annual Leave

Annual leave for your executive isn’t just a personal matter for them — it’s an operational shift for you. For the duration of their absence, you become the keeper of the flame: the first line of defence against creeping chaos, the bridge between in-progress projects and impatient stakeholders, and often the only person who knows the “why” behind what’s happening.

Handled well, you can protect their mental space so they truly switch off, keep business moving without constant escalation, and welcome them back to a calm, well-prepared environment. Handled poorly, they can return to a wall of emails, stalled projects, and an inbox that makes them regret ever leaving in the first place. Even worse, they don’t have a break at all and spend their time away constantly on calls and replying to emails.

This week I break down exactly how to prepare, manage, and wrap up your exec’s annual leave — so you both get the best outcome possible.

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Before They Leave: Setting the Stage for Success

The preparation period is the most important phase. You’re aiming for two outcomes:

1. Your exec feels confident they can unplug without worrying about what’s happening back at HQ.

2. You have all the tools, context, and authority you need to manage things in their absence.

Here’s how to get there.

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1. Have a “Pre-Holiday Wrap-Up” Meeting

Block at least 30–60 minutes with your exec the week before they leave. This is your chance to:

• List all live projects and their current stage.

• Identify deadlines that will fall during their absence (for the above projects, or things like payroll sign off).

• Discuss any meetings or deliverables they won’t be there to handle.

• Flag decisions that might need making — and agree whether you’ll make them, delegate them, or defer until their return.

Pro tip: If your exec is the type to remember things just as they’re heading out the door, keep a running list of “pre-leave loose ends” during the week before. Bring it to the wrap-up meeting so nothing gets missed.

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2. Control the Calendar

You’d be amazed how quickly a “protected” leave period can get chipped away at. Vendors book quick calls, a senior colleague tries to sneak in a catch-up, or a recurring meeting doesn’t get cancelled and pulls them into “just five minutes” of work.

• Block out the full leave period as “OOO” in all shared calendars — no half-days, no “maybe available” notes.